11. Goodfellas (1990)
Another example of one of the best gangster movies of all time finding appeal among those who may not necessarily gravitate towards such films. Goodfellas draws a lot of its energy from the life and times of Henry Hill (played in adulthood by Ray Liotta), which were, if nothing else, some lively times for Hill and everyone in his circle of family and fellow criminals.
The movie also features standout work from Lorraine Bracco, Paul Sorvino, Joe Pesci (who won an Oscar), and Robert De Niro. However, you can make an argument that the real star of this movie is the intensely quotable screenplay, written by Scorsese and Nicholas Pileggi (from Pileggi’s own 1985 nonfiction book), combined with the legendary editing work by the endlessly talented Thelma Schoonmaker.
Watch if: As far back as you can remember, you’ve always wanted to be a gangster.
Avoid if: Joe Pesci scares you to death.
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12. Miller’s Crossing (1990)
Released in the looming shadow that was almost immediately cast by the success of Goodfellas, the Coen Brothers; take on the mob drama was largely ignored in the fall of 1990. It grossed just $5 million against its $14 million budget. Thankfully, like many movies from the Coens, Miller’s Crossing has since founds an appreciative audience.
This story of an enforcer (Gabriel Byrne) for a powerful Irish mob boss (the late, perpetually great Albert Finney) is considerably different from something like Goodfellas. There is a striking noir atmosphere to be found in this film, which also features the trademark, slightly surreal humor of the Coens. Miller’s Crossing also possesses a strange, somewhat disconcerting mysticism. Again, something you often find in the best Coen Brothers movies.
Watch if: You want to see a mob movie unlike any other.
Avoid if: You prefer gunplay over character development.
13. Boyz n the Hood (1991)
“Hood” movies are more often than not gangster movies with predominantly African American casts. This is another offshoot of the larger gangster movie genre where it wouldn’t be difficult to run through a list of 10 or 15 movies. Nonetheless, in the universe of such films, few have the emotional staying power and depth within the violence and ambition that permeates this film.
Boyz n the Hood is also essentially a movie about childhood. It just happens to be one of the most depressing movies about childhood in the history of American cinema. Beyond the themes and powerful story, the film also offers pitch-perfect performances from Laurence Fishburne, Cuba Gooding Jr. Nia Long, Regina King, and Ice Cube.
Watch if: You want to see an unapologetic look at a different brand of gangster cinema.
Avoid if: You need an ending that will surprise you.
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14. American Me (1992)
Edward James Olmos directed and starred in this Mexican mafia epic, which caused considerable controversy with actual Mexican gangs after the fact.
In the present, the film deserves to be considered alongside the many, many gangster movies that were released in this time period. Olmos, who generally has been a distinctive supporting actor, has depth and charisma to spare as the centerpiece for this underrated gem.
At the same time, American Me isn’t just a showcase for Olmos. The film also benefits greatly from an impressive ensemble. All of them help to create an element of authenticity that at least comes through in the film’s tone, and in the various commentaries it showcases with cinematic tension and a fascinating drug kingpin story.
Watch if: You want to see one of the most underrated gangster movies of all time.
Avoid if: Edward James Olmos sans some sort of spaceship is a hard pass for you.
15. Sonatine (1993)
My favorite Takeshi Kitano film, Sonatine is arguably one of the best yakuza movies of all time, as well. Kitano wrote, directed, and starred in this deceptively simple story of a weary yakuza who is forced to hide out at the ocean, after a seemingly minor assignment is beset by a massive spree of violence.
The movie’s tone, which veers between explosions and quiet seaside scenes, dropping even further into even darker territory on a frequent basis, is impossible to get comfortable with. This isn’t a bad thing, as the performances, particularly Kitano’s, are among the most riveting to be found on this list.
Sonatine is also a constant assault on our expectations. When the film in question captivates us with its performances, pace, and writing, such an assault can be an unreal, essential experience.
Watch if: You want to see one of the most consistently surprising gangster movies ever made.
Avoid if: Russian roulette scenes are more than your nerves can stand.
16. Casino (1995)
Beyond Casino, which may be Scorsese’s mob masterpiece, Scorsese has continued telling such stories through the years. He’s getting ready to do another with the upcoming Irishman. Yet Casino still feels like the summation of Scorsese’s ability to craft some of the best underworld movies of all time.
Loosely based on the death of Las Vegas under mob control, Casino is an epic in every sense of the word. The story is an epic, spanning the 70s and early 80s, as well as the personal histories of individuals such as Same “Ace” Rothstein (played to the full extent of his acting powers by Robert DeNiro).
The music and editing feel epic contributions unto themselves. Everything about this film is mythical and spiritual in equal measures, even as it dives tens of millions of miles into one of the most elaborate concepts of Hell ever created.
Casino is at its heart a story of pride, and the impulse to fight reality, or even just the future. The consequences of all those things create one of the top films of the 1990s.
Watch if: You want to see a Scorsese/DeNiro/Pesci collaboration with everyone at the absolute top of their respective crafts.
Avoid if: You are content to never hear the sound of a man being beaten to death with a baseball bat.
17. Snatch (2000)
Snatch can be tough to keep up with sometimes. One of Guy Ritchie’s most satisfying gangster movies moves so deftly and beautifully across memorable characters, hysterical developments, and perfect dialog that it’s easy to feel as though you missed something.
There is always a good chance, when it comes to a crime comedy this layered and fearlessly clever, that you have in fact missed something. Whether it is Jason Statham’s perfect comedy straight man, Brad Pitt in one of those performances that reminds you of his range, or the late Dennis Farina in one of the most satisfying variations of his “New York Asshole” persona, you will feel like something incredible passed by. All while you were paying attention to something else.
Snatch throws a lot at you. All of it is good. Just keep in mind that you probably need to see this more than once.
Watch if: You want a movie that doesn’t sacrifice cleverness for performances, writing, or editing.
Avoid if: You’re scared of Vinnie Jones, and those fiery little angry eyes of his.
18. Sexy Beast (2000)
It’s a weird timeline when Ben Kingsley wins an Oscar for the largely forgettable Gandhi, but doesn’t win one for playing a psychotic, singular British mobster in Jonathan Glazer’s Sexy Beast. While Kingsley’s performance here is the most memorable component, Sexy Beast is also a masterwork of tension and dark comedy.
It also has Ray Winstone as the poor retired gangster who has to put up with Kingsley’s Don Logan, who wants Winstone’s “Gal” to help him with one last job. Few movies, particularly on any list of the best gangster films, have a marriage of violence and humor that exists quite in the fashion you will find here.
Watch if: You want to see Ben Kingsley play one of the most fascinating movie maniacs in recent history.
Avoid if: You already know someone from work who’s a lot like Don, and that’s more than enough for you.
19. City of God (2002)
Set in the Cidade de Deus suburb of Rio de Janeiro, Brazil, City of God is a story somewhat in the tradition of Mean Streets. It can be boiled down to a story of youth coming of age as a criminal organization dominates the culture, the present, and perhaps even the future of a community.
City of God is breathless stuff, featuring an intense pace that works well with a brilliant ensemble cast. Alexandre Rodrigues as the film’s main protagonist is still a performance that can resonate with virtually anyone. City of God is also one of the most hopeful entries on this list.
As you may or may not know, hope figures heavily into many of these stories. It just doesn’t usually work out for anyone.
Watch if: You want to see one of the most stimulating crime dramas of the 21st century.
Avoid if: Brazil doesn’t sound like a very exciting place.
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20. American Gangster (2007)
Leave it to Ridley Scott to prove that American gangster movies can still have something unique to offer as a cinematic experience. While entertaining stories about gangsters are still being told, few of them deviate from the playbook created by the likes of Mario Puzo, Francis Ford Coppola, David Chase, or anyone else who has created a definitive work in this field.
American Gangster gets a lot of its strength from great performances from its massive ensemble cast, including Denzel Washington, Russell Crowe, and Ruby Dee. Yet this somewhat-true story of Harlem drug kingpin Frank Lucas is ultimately an American story. This is perhaps why so many gangster films continue to be made in the United States. We are obsessed by these stories, and the grandeur and power of a movie like American Gangster is ample evidence of that.
Watch if: You want a powerhouse crime epic with one of Denzel Washington’s best performances.
Avoid if: You can’t stand Ridley Scott.
Runners Up
What’s really scary is that even after picking the top gangster movies from film history, we still have dozens of titles leftover. Did your favorite make the list? If not, you may find it below, presented in no particular order.
– Hard Boiled (1992)
– Infernal Affairs (2002)
– My Blue Heaven (1990)
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